Dabbling in DoorDash Delivery: Lessons Learned from Personal Experience

This is an intro and excerpt from the original article posted on donndurante.com.

In the 2023 Dasher Community Impact Report, an estimated 6MM drivers were delivering for DoorDash.

I was one of them.

Why and How It Started

It was Wednesday morning, September 20, 2023 — just after my 54th birthday. I had a dentist appointment first thing in the morning so I let my boss know that I’d be in the office a little later than usual.

When I got to work, even before I sat at my desk, my boss tapped me on the shoulder and asked if I had a few minutes as he led the way to one of our smaller meeting rooms. When I saw that our Head of HR was waiting for us at the table, I knew what was about to happen.

They were both kind, gracious, and professional given the uncomfortable task. I was one of about 10% that they were letting go as part of an organizational restructure. While I still needed a moment to process the reality of the situation, it wasn’t a surprise. I sensed this would happen but didn’t know it would happen so soon.

Layoffs are nothing new to me. I’ve been laid off or fired more than 5 times during my 30+ years after college. I’ve gotten good at landing on my feet. I take advantage of the reset to consider what else I may want to change as I navigate to the next thing. And every iteration has taught me more about what I need and want for that particular season of my life.

Every transition is different. This one led me to DoorDash.

With a severance package and some unemployment benefits, I gave myself about a month or so to plan and get started with something new. Although I had a few solid leads and a promising prospect in the works, November came along and I needed to keep my commitment to start generating immediate income in the interim. Freelance consulting on Fiverr and Amazon affiliate marketing hadn’t generated anything yet. It was time to try something else.

My wife suggested Uber or Lyft, but as an introvert, the idea of sitting in my car with all sorts of strangers didn’t appeal to me. DoorDash, on the other hand, had the paid driving without the passengers. Many deliveries are contactless (“leave at my door”).

It took me less than an hour to sign up, pass the background check, and start dashing.

Test and Learn

In the spirit of dabbling with purpose, I wanted to approach DoorDashing as a learning experience that not only met some short-term financial buffering but also helped me understand what works and what doesn’t for this potential income opportunity. So far, I’m zooming in on the tactical and strategic things that can maximize the benefits of the time spent, but I also zoom out to understand whether or not this is sustainable and aligned with what’s important for the long term.

For me, learning has to have at least some structure to be effective. While I still learn from general trial and error, the lessons take longer to stick and some insights are overlooked. There are various moving parts and variables that can create a lot of noise. Without the structure I created, a simple spreadsheet, I don’t think I would have learned as much as I have in the few months I’ve been dashing so far.

My methodology isn’t very scientific with rigorous controls. I don’t factor in standard deviation or statistical significance, but I’ve tried to apply some level of consistency to uncover general patterns, all the while challenging assumptions and trying to prove myself wrong.

There were times when I found it difficult to note any learnings from a given dash. I could occasionally note some nuance that led to other hypotheses, but after a while, I started seeing more of the same. In these instances, I just remarked that the outcomes and results were consistent with previous findings.

Variables (during any given Dash):

When I dabble and experiment with anything, I like to consider the variables that I have more control over. Some things are outside of my control, but I factor them in as I note my learnings. This is a list of the variables that are top of mind for me.

• Day of the week
• Time of day
• Market and Location
• Number of active Dashers in the area
• Number of active Top Dashers in competition
• Size of orders and offers
• Wait times at stores
• Per Offer vs. By Time
• Scheduled versus unscheduled
• Weather
• Holidays (e.g., Spring Break) and Special Events (e.g., Super Bowl)
• Customers’ cravings, appetite, mood, and level of generosity
• Luck (right place at the right time)

Read more about my takeaways so far including a word of warning for new Dashers.

If you’ve considered becoming a Dasher or are relatively new to DoorDash delivery, the original post continues with tips, lessons learned, and a different perspective from a “Top Dasher”.